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- Newsletter 337: Best Gay Resort Turns Fifty, Get Naked in Bali + Our Italy Cruise & More
Newsletter 337: Best Gay Resort Turns Fifty, Get Naked in Bali + Our Italy Cruise & More

Fifty Years of Bare Excellence: Island House Key West Hits Hot Daddy Status
Officially reaching hot daddy status this year, Island House Key West has hit its 50th anniversary. Since its inception in 1976, the clothing-optional resort for gay men has had countless naked men pass through its doors satisfied (not that it’s one to boast)! With age, they’ve perfected the gay resort experience through their unbeatable facilities, personalized service, and activities that encourage socializing and no-nonsense fun.
Inside, alongside all those aforementioned naked men, you’ll find a gym, multiple Jacuzzis, a sundeck, tropical gardens, and a large pool with a 24-hour poolside café/bar. They provide four free drinks and a happy hour to bring guests together—not to mention its infamous weekly pool parties. The rooms themselves are a study in comfort, with large cozy beds, quirky decorations, and lighting to suit any mood.
Remember, when it comes to gay holiday resorts, experience matters—and daddy always knows best at Island House Resort, the best gay resort in the world.
SPONSORED BY ISLAND HOUSE
This newsletter was written in collaboration with one or more travel brands or businesses. We may receive compensation when you click the links and make a purchase. Read our full advertising policy here.
Bespoke Journeys for Life’s Special Moments. Ursula Hosting, founded by (the very handsome and experienced travel buddy of TBT) Nelson, crafts tailor-made itineraries globally. Honeymoon to Spain or Italy? Reunion in Greece? Or how about Colombia? Nelson and Ursula Hosting will plan your dream trip flawlessly. FOLLOW URSULA HOSTING |
When booking an LGBTQ+ small-group journey, what budget range (per person) feels right for you?Take our poll and help us customize your travel content & experience. Currency in US Dollars. |

Formerly The Naked Paradise Villa, now reinvented as ‘The Naked Bali Experience by Everything to Sea, is exactly what it says it is—both an authentic way to experience the beautiful island of Bali and an opportunity to experience genuine human connection while among naked men in an undeniably gorgeous part of the world.
While your naked adventure on July 11-17, 2026, will be set within a breathtaking villa tucked away in a little pocket of tropical paradise in Bali, the soul of the trip lies in the connections you’ll make while you are there. “Everybody naked and every naked body” is the driving philosophy behind Everything to Sea’s trips. So, in other words, men of all shapes, sizes, and ages are welcome, and your personal, individual journey will be centered around inclusivity, self-discovery, and unfettered freedom.
Taking place on an enclosed private property, the activities within the villa are all designed to make you feel free and safe without clothes and to build comradeship through shared experience. As you shed your clothes, you’ll find that the layers fall away not only from your body, but from your spirit too, leaving you open, present, and free to finally be your full self out in the warm Balinese air.
Lisbon rewards attention. A small cultural gathering is taking shape — shaped by conversation, design, and shared moments. DISCOVER GLAINNE |

A Little Love for Italy on Our New Cruise in August 2026
As the old saying goes, “When in Rome…” hop on a cruise with Two Bad Tourists! At least that’s what we are saying because we’re thrilled to announce our brand-new Sicily, Naples, Cannes & Corsica Cruise, setting sail from Rome (Civitavecchia) on August 22-31, 2026. Join our gay group aboard a Virgin Voyages vessel for ten days at six ports around the coast of Italy with eclectic entertainment, group dinners, parties, and plenty of surprises aboard too.
The first stop is Catania, the jewel of Sicily and star of White Lotus, where dramatic landscapes meet irresistible charm. Next, we head north to Naples, a lively city filled with UNESCO-listed historic streets, bustling piazzas, and rich Baroque treasures. From there, it’s on to Ajaccio in Corsica, the French-speaking island that blends Mediterranean beauty with Napoleonic heritage. Then we’ll soak up the glamour of Cannes, France’s sophisticated playground of the rich and famous. Finally, we return to Italy at Livorno, the gateway to two Tuscan gems: Pisa and Florence, before looping back to Rome.
Get on board with us as we give Italy the spicy loving it deserves!
SPECIAL OFFER!
For solos: join for just $2,250 and get a private cabin.
For couples & friends: Book a Sea Terrace cabin by February 23 and save 10%. That’s just $2,203 per person.
Book Dodie in Bali, Oskar in Mexico City, Sebastian in Lima, or one of our other Holiday Houseboys in 175 destinations worldwide. A Holiday Houseboy is a gay friendly tour guide who looks after your safety and welfare at all times. Contact Alan on WhatsApp +94 76 630 1069 for more info. VISIT WEBSITE |

Men on the Prowl – The Definitive Guide to Cruising in Europe's Three Most Sex-Positive Cities
Lone wolves on the hunt for men on their European travels aren’t at a loss for options.
The silver lining from years of discrimination driving gay/bi/queer men looking for companionship underground is that we now have saunas, cruising bars, fetish clubs, darkrooms, and the more clandestine options of parks, woods, and abandoned industrial sites as our hunting grounds. Interestingly, the rise of cruising apps has done little to affect this, showing that it’s the thrill of the hunt and heading out into the wilderness that still appeals to many.
When traveling, there’s no reason one can’t go sightseeing in the day and then get to know the locals by night, for the fully rounded experience. This is your definitive guide to the three best cities in Europe to get some action.
Getaway on a Whim. Spontaneous travel is a lot of fun, and Whimstay makes last-minute getaways easy and affordable. With great rates and quality stays, you can book everything from San Diego condos to Norway cabins or Vegas houses—flexible, stylish options that make saying “yes” to travel effortless. BOOK YOUR GETAWAY |

Gay Travel Guide to Buenos Aires
Argentina's charismatic capital blends European charm with Latin American flair, earning it the nickname the “Paris of South America”. Buenos Aires is a city infused with every bit as much passion as Madonna belted out Don't Cry For Me Argentina from the balconies of the Casa Rosada during the iconic film Evita.
What's more LGBTQ+ rights in Argentina are quite advanced compared to the rest of the continent, and Buenos Aires in particular has a flourishing gay scene. Oh and there's a superabundance of friendly, beautiful men in the city. Just in case you needed another reason to add Buenos Aires to your Latin America travel plans.
From Athens to Barcelona. Join us on our gay group cruise from October 4-11, 2026, voyaging all the way from Athens to Barcelona with stops in Mykonos, Sicily, the Amalfi Coast, and Rome. Enjoy themed parties, group dinners, shore excursions, and more! SPECIAL OFFER! Solo travelers pay just $2,240 for a private cabin. BOOK NOW |
Are you or someone you know planning to visit Amsterdam in the next 12 months?Take our poll and help us customize your travel content & experience. |
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